


Are You Experienced?

by Amelia_Clark



Category: Supernatural
Genre: Anal Sex, Angst, Character Study, Consensual Underage Sex, Deleted Scenes, Episode: s09e06 Heaven Can't Wait, F/M, Headcanon, Loss of Virginity, M/M, Oral Sex, Pre-Series, Prostitution, Sex Work, Underage Prostitution, part 2 is the upsetting one
Language: English
Status: Completed
Published: 2015-01-16
Updated: 2015-01-16
Packaged: 2018-03-07 20:38:33
Rating: Mature
Warnings: Underage
Chapters: 1
Words: 2,470
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/3182363
Author URL: https://archiveofourown.org/users/Amelia_Clark/pseuds/Amelia_Clark
Summary: <blockquote class="userstuff">
              <p>Five vignettes from Dean Winchester's sexual history.</p>
            </blockquote>





	Are You Experienced?

**Author's Note:**

> This fic is both my headcanon for Dean's sexual history and a belated entry to the 9.06 fanfic gap genre.

1.

The first time Dean Winchester gets laid, he’s sixteen.

After leaving Robin without even saying goodbye, he figures there’s no point in trying anymore to have a girlfriend, go on dates, all that normal shit. He’s a hunter, and hunters can’t do any of that. He knows his dad picks up women on the road sometimes, comes back to the motel room smelling like perfume—why not follow his lead, like he always does?

So the next high school he’s at, somewhere in Michigan, he listens to the guys talking about which girls are easy, then finds the easiest—a girl named Jennifer—and asks her to a movie.

Jennifer, who prefers Jen to Jenny, who’s a grade ahead of him and cute as hell, with a ready smirk and dyed-red hair. He’s pretty sure she knows exactly what he’s after; and sure enough, during the second preview her tongue is already in his mouth. She jacks him off while a square-jawed action hero battles bad guys onscreen. It’s the most amazing thing that’s ever happened to him.

Her mom works nights, so Jen brings him back to her place after the movie and takes off his clothes on the couch, shows him how to roll on a condom and rides him till his eyes roll back in his head.

They fuck pretty constantly the month he’s in town. She’s a lot of fun, actually, and couldn’t give less of a shit about her rep: “I like sex,” she says, tugging his jeans open, “anybody’s got a problem with that they don’t have to sleep with me.” He learns a lot from her—how to go down on a girl, how to make her come when he’s inside her. He tells her he’s leaving, and she just smiles and tells him to take care.

He never sees her again.

2.

The first time Dean gives a blow job, he’s seventeen.

He hasn’t seen his dad in ten days; the money ran out two days ago, and Dean hasn’t eaten since then, lying to Sammy about it. The kid’s still growing, he needs the food more than Dean does. Not like it’s the first time he’s gone hungry.

When there’s really nothing left, he pockets one of his fake IDs and heads to a dive bar to hustle pool. He misjudges his mark—the guy is really fucking good—and ends up losing, badly, and taking the beating when his opponent realizes he’s got nothing to pay him with.

He’s in the single-stall bathroom washing the blood from his face when there’s a knock. “Fucking occupied!” he yells, and a male voice says “I know, lemme in anyway.”

Fine, not like the night can get worse. The dude who walks in and locks the door again behind him is mid-40s, probably a trucker, with a ponytail that doesn’t distract at all from his bald spot. “Hey kid,” he says. “You OK?”

“I’ll be fine,” Dean says, scowling. “Why the fuck do you care?”

“You ain’t got a dime, do ya?” Dean shakes his head. “Tell ya what, kid. Been looking at that pretty mouth all night—I’ll give you forty bucks to suck my dick.”

“What? No fucking way,” says Dean. “Get the fuck outta here.”

The dude doesn’t leave, just stares Dean down. He knows he’s desperate—Dean could buy food with that forty bucks, feed him and Sammy for another week if Dad doesn’t show up. Maybe it won’t be that bad.

So Dean drops to his knees in the bathroom and undoes the dude’s fly.

After that, he does it every now and then when times are tough. It doesn’t take as long as a pool hustle, and provided the guy’s showered recently, it really isn’t that bad. Weird, yeah, and Dad would kill him if he ever found out, but he thinks of it the same way he does fixing a car—just work, just something he knows how to do. And sometimes, kneeling in an alley or a truck stop stall, he wonders what it would be like to do this with someone who knows his name.

3.

The first time Dean blows a guy for free, he’s twenty-two.

It’s a week after Sammy left for Stanford, and Dad hasn’t said a word about it—hasn’t said a word to Dean at all, in fact. He blames him somehow, and Dean’s pretty sure he’s right, he just can’t figure out how. But most things are his fault, so Sammy leaving probably is too.

One night he’s three drinks in before he realizes he’s in a gay bar. He’s not sure which would make Dad angrier: that he’s hanging out with a bunch of queers, or that he had so little awareness of his surroundings. But he doesn’t leave. He went out to get laid tonight—maybe he could do a guy instead of a girl. It wouldn’t make him gay. It’d just be a thing he did, like blowing those truckers; it wouldn’t mean anything at all.

“Can I buy you a drink?” someone says, and Dean turns to see a dude about his age with shoulder-length reddish hair and big brown eyes. He’s tall and rangy and seems so comfortable in his own skin; mouth dry, Dean nods and accepts a beer.

The dude sits down next to him. “I’m Eric,” he says.

“Dean.” They shake hands, and the bartender comes back with Dean’s beer; he sips nervously, not sure what to do next.

“You live around here?” Eric asks.

“Nah, just passing through.”

“Same,” says Eric. Turns out he’s a baseball player, left field for some extremely minor-league team, and he’s remarkably easy to talk to. Dean almost feels like he’s on a regular date, getting to know someone over drinks. 

Dean’s just drained his beer when Eric leans over and kisses him. He startles for a second, but it’s not like he didn’t know where this was headed, and it’s nice. Dean loves kissing, always has, and Eric’s mouth is soft and warm. He tangles one hand in Eric’s hair and kisses back.

“You wanna get outta here?” Eric asks when he pulls away.

Eric’s room’s about as shitty as Dean’s own—he thinks it’s even the same bedspread that they tumble onto. Eric gets him off first, ginger curls brushing Dean’s bare thighs while his head bobs on Dean’s cock. Then Dean flips them, swallows Eric down, and it is different when it’s not a transaction. He’s usually quick and dirty about it, but he slows down to savor it, the weight of Eric’s dick on his tongue, Eric’s hand on the back of his head, urging him closer without forcing him.

“I’m not gay,” Dean says suddenly in the afterglow.

“Neither am I,” says Eric.

“Uh, I got news for you, buddy, you just came in a dude’s mouth.”

“So did you,” Eric says with a shrug. “You fuck women too, I take it?” Dean nods. “So do I, because we’re both bi.” When Dean just stares at him blankly, Eric clucks his tongue and explains, “Bisexual, Dean. You didn’t know that was a thing?”

No, he didn’t. Dean’s never even heard the word before, and he feels stupid as hell about it, that he could be something and not even know it.

He tries out the word while he walks back to his own room, mumbling it over and over until it rolls off his tongue sweet as pie.

4.  
The first time Dean has a dick up his ass, he’s got six months to live.

He stopped picking up guys when he started traveling with Sam. Sure, Mr. College Boy probably knew some dudes at Stanford who weren’t straight as an arrow, but it’s not a conversation he wants to have with his little brother, ever if he can help it.

But after his death sentence, he figures why not? He misses messing around with dudes, and he’s never taken that last step into actual, full-on fucking. He’s done anal with a few girls over the years, and they didn’t hate it; and he’s watched enough gay porn by now he knows it’s better for guys. Something up there called the prostate, can make you see stars if it’s done right.

So one night he tells Sammy not to wait up—not an unusual request these days—and he finds a gay bar near the local college campus, lets himself get picked up by a guy named Christian with glasses and a booming laugh. He’s working on a dissertation on the Roman novel, and he’s possibly the smartest person Dean’s ever talked to. 

Certainly the smartest ever to have his hands down Dean’s pants, as they grind together in the kitchen of his tiny grad-student apartment. Dean blurts out between kisses that he’d like to be fucked, and Christian groans into his ear. “You’ve bottomed before?” he asks.

“Uh, no,” says Dean. “But I want to. I really, really do.”

“All right,” Christian says after a moment. “I can work with that.”

He strips Dean in the bedroom and tells him to get on all fours, parts Dean’s cheeks and runs a thumb over his asshole. Dean shivers. “Never been fingered either?” asks Christian, and Dean stammers a negative. “I’ll go slow. Keep me posted on how you’re feeling.”

Eventually, there’s the crinkle of a condom wrapper, and Dean blinks down at the rumpled sheets while Christian slides into him, a little at a time, until he’s fully sheathed and draped over Dean’s back. “You OK?” he asks, kissing Dean’s neck.

Dean whimpers. It’s a good whimper, a “yes” whimper, and he gets out words to that effect before Christian starts to move, and goddamn but Dean waited too long for this, he should’ve been doing this for years. “Fuck me,” Dean whispers to the mattress, and then he says it again, louder, as Christian speeds up. “Fuck me harder.”

Dean stays the night, wakes up as the little spoon and doesn’t even mind.

5.  
The first time Dean has sex with Cas, he’s thirty-four.

He can’t let Cas sleep on a gas station floor—the thought’s unbearable, the guilt of it acid in his mouth. “Wanna hang out in my motel room?” he asks. “TV, pizza, pick up a six-pack?”

“If you’d like,” Cas says. He’s angled away from Dean, staring blankly out of the passenger-side window. Dean can see the ridge of his collarbone where his shirt’s unbuttoned. He wants to put his mouth on it.

Instead, he licks his lips and says, "Sorry your date fell through."

"It's fine," says Cas. "I'll be fine."

"Dammit, Cas, that bastard Ephraim was here for a reason. You're not fine, and, uh, we should talk about it." But it's Dean's fault, really, that Cas bottles things up like this. Because it's his own M.O., and who else does Cas have as a model for humanity?

"Talking won’t help, Dean," says Cas wearily. "I'd just like to sleep, honestly. Thank you for offering me a place to stay for the night."

"Yeah, any time, buddy," Dean says before he realizes what a dumbass statement it is. Cas had had a place to sleep, and then Dean chucked him out without even telling him why.

Cas doesn't call him out, though. Instead, they drive in silence to Dean's room at the Bluebird Inn, and Dean flips on the TV while Cas looks around for someplace to sit—the place is too cheap to have a chair, so there's really only the bed. Dean gestures to it awkwardly. "Go for it, dude, I'll sleep on the floor."

A flicker of something passes across Cas's face; Dean would think it was disappointment if he didn't know better. "What do you want on your pizza?" he asks, and Cas shrugs.

"I don't know," he says. "The cheese slice at the Gas 'n' Sip is...uninspiring."

Dean's eyes go wide. "You've only had gas station pizza? Damn, we gotta fix that, Cas. Pizza is nature's perfect food." 

"Pizza is a human construct, Dean. It doesn't exist in nature," Cas says with a frown, and Dean laughs in relief: this is the dorky-ass angel he remembers. 

"There you are," Dean says, patting him on the shoulder. "Knew you were in there somewhere. C'mon, I'll order us up a supreme, make a beer run. Take your shoes off and kick back, OK?"

And Cas obeys; when Dean returns with booze in hand, Cas has made himself a nest of pillows against the headboard and is half-watching _The Bachelorette_ with one socked foot crossed over the other. Dean cracks open two beers and offers him one, and Cas drains half of it with a long swallow; watching Cas’s throat work, Dean sips his own beer hurriedly to clear the sudden dryness in his mouth.

“Mind if I sit?” Dean says, and Cas nods; keeping a careful two feet between them, Dean stretches his legs out on the mattress. “Lemme see that hand.”

The cut on Cas’s palm is pretty shallow, but his wrist is definitely sprained—Cas winces when Dean bends it, holds his breath while Dean wraps it deftly. “Here,” he says, pressing his cold beer bottle against the swollen joint. “Feel good?”

Cas looks at him, then down at their hands, and Dean realizes he’s been brushing his thumb gently along the cut, letting his fingers slip between Cas’s own. “Yes,” says Cas. “That feels good.”

They’re having a moment, one in a long succession of moments, and Dean could ignore or deflect it like he always does. But Cas is human now, they’re equals, and what if he never gets to do this again? So Dean closes his eyes, leans over and kisses him.

And keeps on kissing him, opening his mouth to the nudge of Cas’s tongue, whimpering softly when Cas’s other hand comes up to the back of his neck.

“Do you wanna fuck?” Dean asks when Cas pulls away, his eyes bright.

“You’ll still leave in the morning,” says Cas.

“Yeah. I have to, Cas, it’s not—no one wants you back home more than me, it’s just complicated.”

“Home,” says Cas bitterly. “I can’t go home. Either of them.”

“I’m sorry,” says Dean, moving away. “Fuck, I’m sorry, I shouldn’t have—I won’t do it again.”

He’s about to stand up when Cas lunges for him, presses him down into the bed with all his weight and licks into his mouth again. “We can do it, Dean,” he murmurs, and kisses the hinge of his jaw. “Please, I want to.”

Dean laughs. “Turn off the TV,” he says, and talks Cas through laying him down and screwing him slow.

It’s the most amazing thing that’s ever happened to him.


End file.
